1-苯基-3-(5-苯基吡啶-2-基)脲 | 1044239-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1-苯基-3-(5-苯基吡啶-2-基)脲
• 英文名称: 1-phenyl-3-(5-phenylpyridin-2-yl)urea
• CAS: 1044239-15-7
• 化学式: C₁₈H₁₅N₃O
• 分子量: 289.337
• InChiKey: XYJLQPYKZPZXQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-5-苯基吡啶 在 potassium phosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1-苯基-3-(5-苯基吡啶-2-基)脲
  参考文献：
  名称：

  由2-氨基吡啶鎓盐无金属合成吡啶-2-基脲

  摘要：

  通过2-氨基吡啶鎓盐和芳基胺的反应合成吡啶-2-基脲衍生物，已经开发出了前所未有的碱促进多米诺骨牌方法。所开发的策略可耐受各种官能团，并以中等至良好的产率提供吡啶-2-基脲。假定该反应涉及串联环化，分子间亲核加成，开环和去甲基化。

  DOI：

  10.1016/j.tetlet.2019.07.030

文献信息

• False Positives in a Reporter Gene Assay: Identification and Synthesis of Substituted <i>N</i>-Pyridin-2-ylbenzamides as Competitive Inhibitors of Firefly Luciferase
  作者：Laura H. Heitman、Jacobus P. D. van Veldhoven、Annelien M. Zweemer、Kai Ye、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm8004509

  日期：2008.8.1

  Luciferase reporter-gene assays are a commonly used technique in high-throughput screening campaigns. In this study, we report on a luciferase inhibitor (1), which emerged from an antagonistic G protein-coupled receptor luciferase reporter-gene assay screen. Instead of displaying receptor activity, compound I was shown to potently inhibit luciferase in an in vitro enzymatic assay with an IC50 value of 1.7 +/- 0.1 mu M. In addition, 1 was a competitive inhibitor with respect to the substrate luciferin. A database search yielded another inhibitor (3) with a similar N-pyridin-2-ylbenzamide core. Subsequently, several analogues were prepared to investigate the structure-activity relationships of these luciferase inhibitors. This yielded the most potent inhibitor of this series (6) with an IC50 value of 0.069 +/- 0.01 mu M. Further molecular modeling studies suggested that 6 can be accommodated in the luciferin binding site. This paper is meant to alert users of luciferase reporter-gene assays for possible false positive hits including highly "druglike" molecules due to direct luciferase inhibition.
• Metal-free synthesis of pyridin-2-yl ureas from 2-aminopyridinium salts
  作者：Saroj、Om P.S. Patel、Krishnan Rangan、Anil Kumar

  DOI：10.1016/j.tetlet.2019.07.030

  日期：2019.8

  domino approach has been developed for the synthesis of pyridin-2-yl urea derivatives via the reaction of 2-aminopyridinium salts and arylamines. The developed strategy tolerated a wide range of functional groups and afforded pyridin-2-yl ureas in moderate to good yields. The reaction was postulated to involve tandem cyclization, intermolecular nucleophilic addition, ring opening, and demethylation.

  通过2-氨基吡啶鎓盐和芳基胺的反应合成吡啶-2-基脲衍生物，已经开发出了前所未有的碱促进多米诺骨牌方法。所开发的策略可耐受各种官能团，并以中等至良好的产率提供吡啶-2-基脲。假定该反应涉及串联环化，分子间亲核加成，开环和去甲基化。